139719-06-5

Basic information

• Product Name: 4-chloro-N-(4-hydroxy-1-naphthyl)benzenesulfonamide
• Synonyms: 4-chloro-N-(4-hydroxy-1-naphthyl)benzenesulfonamide
• CAS NO: 139719-06-5
• Molecular Formula: C₁₆H₁₂ClNO₃S
• Molecular Weight: 333.78938
• Mol File: 139719-06-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-chloro-N-(4-hydroxy-1-naphthyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-N-(4-hydroxy-1-naphthyl)benzenesulfonamide(139719-06-5)
• EPA Substance Registry System: 4-chloro-N-(4-hydroxy-1-naphthyl)benzenesulfonamide(139719-06-5)

Safety Data

• Hazardous Substances Data: 139719-06-5(Hazardous Substances Data)

Upstream product

• 2834-90-4 4-amino-1-naphthol 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 236739-38-1 4-chloro-N-(2,3-dibromo-4-oxo-3,4-dihydro-2H-naphthalen-1-ylidene)-benzenesulfonamide 
• 86-57-7 1-Nitronaphthalene 
• 605-62-9 4-nitro-1-naphthol 

Downstream Products

• 13243-65-7 2,3-Dibromo-1,4-naphthoquinone 
• 152509-82-5 N-p-chlorobenzenesulfonyl-2-bromo-1,4-naphthoquinone imine 
• 139719-09-8 4-Chloro-N-[2,3-dichloro-4-oxo-4H-naphthalen-(1E)-ylidene]-benzenesulfonamide 
• 107379-25-9 4-chloro-N-(3-chloro-4-oxonaphthalen-1(4H)-ylidene)benzenesulfonamide 
• 236739-35-8 4-chloro-N-(2,3,3-trichloro-4-oxo-3,4-dihydro-2H-naphthalen-1-ylidene)-benzenesulfonamide 
• 139719-07-6 4-Chloro-N-(3-chloro-4-hydroxy-naphthalen-1-yl)-benzenesulfonamide 

Relevant articles and documents

Discovery of N-(3-((7H-purin-6-yl)thio)-4-hydroxynaphthalen-1-yl)- sulfonamide derivatives as novel protein kinase and angiogenesis inhibitors for the treatment of cancer: Synthesis and biological evaluation. Part III

A novel series of N-(3-((7H-purin-6-yl)thio)-4-hydroxynaphthalen-1-yl)- sulfonamides were designed and synthesized. Biological characterization revealed that several compounds exerted enhanced anti-proliferative activity against human umbilical vein endothelial cells (HUVECs) and several cancer cell lines and high specific protein kinase and angiogenesis inhibitory activities. Compared with our previously synthesized compounds, the substitution of sulfonamide structure for amide fragment played an essential role for the advance of inhibitory activities. In addition, the replacement of 1H-1,2,4-triazole ring by 7H-purine did not result in obvious decrease of inhibition efficacy, indicating that the sulfonamide structure contributes even more to the inhibition efficacy than the 1H-1,2,4-triazole ring. Among these compounds, compound 9n demonstrated comparable in vitro antiangiogenic activities to pazopanib in both HUVEC tube formation assay and the rat thoracic aorta rings (TARs) test. Meanwhile, compound 9n was identified to inhibit Akt1 (IC50 = 1.73 μM) and Abl tyrosine kinase (IC50 = 1.53 μM) effectively.

Some reactions of new semiquinoid compounds derived from N-arylsulfonyl-p-quinonimines

Polyhalogenated semiquinoid compounds on the basis of N-arylsulfonyl-p-quinonimines react with reducing agents (zinc or sodium dithionite in acetic acid) with elimination of one or two hydrogen halide molecules, depending on the number of hydrogens at the sp3-hybridized carbon atoms, to give the corresponding benzoid structures. Dehydrohalogenation of the title compounds in chloroform in the presence of triethylamine leads to formation of quinonimines. N,N′-Bis(arylsulfonyl)-p-quinonediimine derivatives do not undergo dehydrohalogenation. Reactions with dialkyl hydrogen phosphites result mostly in 1,2-addition and formation of phosphorylated products; the reaction is likely to involve intermediate dehydrohalogenation to the corresponding quinonimines which can be isolated in the pure state.

CHLORINATION OF N-ARYLSULFONYL-1,4-AMINONAPHTHOLS AND N-ARYLSULFONYL-1,4-NAPHTHOQUINONE 4-IMINES

The final products from the chlorination of N-arylsulfonyl-1,4-aminonaphthols and N-arylsulfonyl-1,4-naphthoquinone 4-imines are 4-arylsulfonylimino-1-oxo-2,2,3,3,-tetrachloro-1,2,3,4-tetrahydronaphthalenes.